WO2013100538A1 - Composé pour dispositif opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant l'élément électroluminescent organique - Google Patents

Composé pour dispositif opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant l'élément électroluminescent organique Download PDF

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WO2013100538A1
WO2013100538A1 PCT/KR2012/011429 KR2012011429W WO2013100538A1 WO 2013100538 A1 WO2013100538 A1 WO 2013100538A1 KR 2012011429 W KR2012011429 W KR 2012011429W WO 2013100538 A1 WO2013100538 A1 WO 2013100538A1
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김형선
박무진
유은선
채미영
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제일모직 주식회사
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Definitions

  • the present invention relates to a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having excellent life, efficiency, electrochemical stability, and thermal stability, an organic light emitting device including the same, and a display device including the organic light emitting device.
  • An organic optoelectric device refers to a device requiring charge exchange between an electrode and an organic material using holes or electrons.
  • Organic optoelectronic devices can be divided into two types according to the operation principle.
  • excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is an electronic device of the form.
  • the second is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • Examples of an organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic photo conductor drum, and an organic transistor, all of which are used to inject or transport holes or electrons to drive the device. Injection or transport materials, or luminescent materials.
  • organic light emitting diodes are attracting attention as the demand for flat panel displays increases.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • Such an organic light emitting device converts electrical energy into light by applying a current to an organic light emitting material, and has a structure in which a functional organic material layer is inserted between an anode and a cathode.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
  • the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.
  • the host / dopant system can be used as a light emitting material.
  • materials constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • a hole injection material such as a hole transport material, a light emitting material, an electron transport material, an electron injection material, a host and / or a dopant in the light emitting material, etc.
  • This stable and efficient material should be preceded, and development of a stable and efficient organic material layer for an organic light emitting device has not been made yet, and therefore, development of new materials is continuously required.
  • the necessity of such a material development is the same in the other organic optoelectronic devices described above.
  • the low molecular weight organic light emitting diode is manufactured in the form of a thin film by vacuum evaporation method, so the efficiency and lifespan performance is good, and the high molecular weight organic light emitting diode using the inkjet or spin coating method has low initial investment cost. Large area has an advantage.
  • Both low molecular weight organic light emitting diodes and high molecular weight organic light emitting diodes are attracting attention as next-generation displays because they have advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
  • advantages such as self-luminous, high-speed response, wide viewing angle, ultra-thin, high definition, durability, and wide driving temperature range.
  • LCD liquid crystal display
  • the response speed is 1000 times faster than the LCD in microseconds, it is possible to implement a perfect video without afterimages. Therefore, it is expected to be spotlighted as the most suitable display in line with the recent multimedia era.
  • the luminous efficiency In order to increase the size, the luminous efficiency must be increased and the life of the device must be accompanied. In this case, the light emitting efficiency of the device should be smoothly coupled to the holes and electrons in the light emitting layer.
  • the electron mobility of the organic material is generally slower than the hole mobility, in order to efficiently combine holes and electrons in the light emitting layer, an efficient electron transport layer is used to increase the electron injection and mobility from the cathode, It should be able to block the movement of holes.
  • a compound for an organic optoelectronic device which can play a role of hole injection and transport or electron injection and transport, and can act as a light emitting host with an appropriate dopant.
  • An organic light emitting diode having excellent lifespan, efficiency, driving voltage, electrochemical stability, and thermal stability and a display device including the same are provided.
  • a compound for an organic optoelectronic device represented by the following Chemical Formula 1 is provided.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene
  • the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following Formula 2.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene
  • Ar 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted Dibenzofuranyl group or a combination thereof.
  • Ar 3 may be hydrogen.
  • Ar 2 may be selected from any one of the following Formulas S-1 to S-5.
  • R 1 to R 4 are independently hydrogen, deuterium, C1 to C30 alkyl group, C6 to C30 aryl group Or a combination thereof, in Formulas S-3 and S-4, any one of R 1 to R 4 represents a binding position, and in Formula S-5, any one of R 1 to R 3 represents a binding position. Indicates.
  • Ar 3 may be selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted triphenyl group.
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula 3.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 to R 5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula 4.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 to R 5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula 5.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 to R 5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-1.
  • X 1 to X 8 are each independently, -CR'- or N, and R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, at least one of X 1 to X 3 is N, and at least one of X 4 to X 8 is N.
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-2.
  • X 1 to X 3 are each independently, -CR'- or N, wherein R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and at least one of X 1 to X 3 is N.
  • the compound for an organic optoelectronic device may be represented by the formula A-1 to A-36.
  • the compound for an organic optoelectronic device may be represented by the following formula B-1 to B-96.
  • the compound for an organic optoelectronic device may be represented by the formula C-1 to C-49.
  • the compound for an organic optoelectronic device may be represented by the following formula D-1 to D-20.
  • the compound for an organic optoelectronic device may be a triplet excitation energy (T1) 2.0 eV or more.
  • the organic optoelectronic device may be selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, and an organic memory device.
  • the organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode
  • at least one of the organic thin film layer is the above-described organic optoelectronic device It provides an organic light emitting device comprising a compound for.
  • the organic thin film layer may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof.
  • the compound for an organic optoelectronic device may be included in a hole transport layer or a hole injection layer.
  • the compound for an organic optoelectronic device may be included in a light emitting layer.
  • the compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material in the light emitting layer.
  • a display device including the organic light emitting diode described above is provided.
  • Such a compound can be used as a hole injection / transport material, a host material, or an electron injection / transport material for the light emitting layer.
  • the organic optoelectronic device using the same has excellent electrochemical and thermal stability, and has excellent life characteristics, and may have high luminous efficiency even at a low driving voltage.
  • 1 to 5 are cross-sectional views illustrating various embodiments of an organic light emitting device that may be manufactured using a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • hole injection layer 230 light emitting layer + electron transport layer
  • substituted unless otherwise defined, at least one hydrogen of a substituent or a compound is a deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C10 such as C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group, trifluoromethyl group, etc.
  • substituted halogen, hydroxy, amino, substituted or unsubstituted C1 to C20 amine group, nitro group, substituted or unsubstituted C3 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to Two adjacent substituents of C1 to C10 trifluoroalkyl group or cyano group such as C30 cycloalkyl group, C6 to C30 aryl group, C1 to C20 alkoxy group, fluoro group and trifluoromethyl group may be fused to form a ring. .
  • hetero means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the remainder is carbon.
  • an "alkyl group” means an aliphatic hydrocarbon group.
  • the alkyl group may be a "saturated alkyl group” that does not contain any double or triple bonds.
  • the alkyl group may be branched, straight chain or cyclic.
  • Alkenylene group means a functional group consisting of at least two carbon atoms of at least one carbon-carbon double bond
  • alkynylene group means at least two carbon atoms of at least one carbon-carbon triplet. It means a functional group consisting of a bond.
  • the alkyl group may be an alkyl group that is C1 to C20. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group has 1 to 4 carbon atoms in the alkyl chain, i.e., the alkyl chain is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • the alkyl group is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohex It means a practical skill.
  • Aromatic group means a functional group in which all elements of the functional group in the ring form have p-orbitals, and these p-orbitals form conjugation. Specific examples include an aryl group and a heteroaryl group.
  • aryl group includes a monocyclic or fused ring polycyclic (ie, a ring that divides adjacent pairs of carbon atoms) functional groups.
  • Heteroaryl group means containing 1 to 3 hetero atoms selected from the group consisting of N, O, S and P in the aryl group, and the rest are carbon. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
  • the carbazole derivative refers to a structure in which a nitrogen atom of a substituted or unsubstituted carbazolyl group is substituted with a hetero atom or carbon instead of nitrogen.
  • Specific examples thereof include dibenzofuran (dibenzofuranyl group), dibenzothiophene (dibenzothiophenyl group), fluorene (fluorenyl group) and the like.
  • the hole characteristic means a characteristic that has conductivity characteristics along the HOMO level to facilitate the injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer.
  • an electronic characteristic means the characteristic which has electroconductive characteristic along LUMO level, and facilitates the injection of the electron formed in the cathode into the light emitting layer, and the movement in the light emitting layer.
  • Compound for an organic optoelectronic device is a substituted or unsubstituted aryl group is bonded to the nitrogen of the substituted or unsubstituted carbazole, substituted or unsubstituted pyridinyl group, substituted or unsubstituted in the carbazole It may have a core structure in which a substituted pyrimidinyl group or a substituted or unsubstituted triazinyl group is bonded.
  • the substituted or unsubstituted carbazole is a compound having both hole properties and electronic properties. More specifically, hole properties may be slightly better than electronic properties. However, this may be controlled by a substituent attached to the carbazole.
  • the substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, or substituted or unsubstituted triazinyl group is a substituent having excellent electronic properties.
  • the electronic and hole properties of the entire compound may be adjusted.
  • the core structure may be used as a light emitting material, a hole injection material or a hole transport material of an organic optoelectronic device.
  • it may be suitable for the light emitting material.
  • At least one of the substituents bonded to the core may be a substituent having hole characteristics. Therefore, the compound may satisfy the conditions required in the light emitting layer by reinforcing hole characteristics in the core structure. More specifically, it can be used as a host material of the light emitting layer.
  • the compound for an organic optoelectronic device may be a compound having various energy band gaps by introducing a variety of other substituents to the substituents substituted in the core portion and the core portion.
  • the hole transport ability or electron transfer ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent in organic chemical and thermal stability It is possible to improve the life characteristics when driving the device.
  • the compound for an organic optoelectronic device may be a compound for an organic optoelectronic device represented by the following formula (1).
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof .
  • the compound for an organic optoelectronic device due to the substituent is light emitting, hole or electronic properties; Membrane stability; Thermal stability and high triplet excitation energy (T1).
  • L is a single bond, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl Or a combination thereof.
  • the L may be selectively adjusted to determine the conjugation length of the entire compound, and the crystallinity and solubility of the entire compound may be adjusted according to the binding position.
  • the L include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a dibenzopurenylene group, a dibenzothiophenylene group, a thiophenylene group, and the like.
  • Ar 1 may be a substituted or unsubstituted C6 to C30 aryl group.
  • Specific examples of Ar1 may include a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or And an unsubstituted triphenylenyl group.
  • Ar 1 Due to the presence of Ar 1 it is possible to improve the thermal stability of the compound and to control the degree of packing between the compounds, thereby controlling the intermolecular stacking.
  • Ar 1 may be a substituted or unsubstituted triphenylenyl group. Since the substituted or unsubstituted triphenylenyl group has a bulky structure and produces a resonance effect, the substituted or unsubstituted triphenylenyl group has an effect of suppressing side reactions that may occur in the solid state, thereby increasing the performance of the organic light emitting device.
  • the triphenylenyl group has a wider bandgap and a triplet excitation energy, so that the triphenylenyl group does not reduce the bandgap or triplet excitation energy of the compound by binding to carbazole, and thus has a greater advantage.
  • the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following Formula 2.
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 and R 2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero An arylene
  • Ar 3 is more specifically substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted triphenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzothiophenyl group, substituted Or an unsubstituted dibenzofuranyl group or a combination thereof.
  • Ar 3 when Ar 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted triphenyl group, the effect of substituting the most reactive 3 position in carbazole can be expected.
  • stable aromatic compounds improvements in thermal stability and glass transition temperature due to molecular weight increase can be expected.
  • bulky aromatic substituent the non-planarity of the material can be improved, and the effect of inferior crystallinity can be expected.
  • Ar 3 is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzofuranyl group, hole injection and transport which may be insufficient with carbazole alone Increasing the role allows the entire compound to exhibit bipolar properties.
  • the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following formula (3).
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 to R 5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group
  • the carbazolyl derivative has a hole property as shown in Formula 3, since the carbazolyl derivative has hole properties, the hole injection and transport properties of the entire compound may be improved, and thus the electron and hole properties may be appropriately controlled. .
  • the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following formula (4).
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 to R 5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group
  • the compound for an organic optoelectronic device represented by Formula 1 may be represented by the following formula (5).
  • Ar 1 is a substituted or unsubstituted C6 to C30 aryl group
  • Ar 2 is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group
  • R 1 to R 5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof
  • L is a single bond, substituted or unsubstituted C2 to C10 alkenylene group, substituted or unsubstituted C2 to C10 alkynylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C2 to C30 hetero Arylene group
  • the binding position of the bicarbazole structure is the third position of each carbazole as shown in Formula 5, it may be advantageous in terms of ease of synthesis and increasing stability of the compound by replacing the third position, which is more reactive than the other positions. have.
  • Ar 2 may be selected from any one of the following Formulas S-1 to S-5.
  • R 1 to R 4 are independently hydrogen, deuterium, C1 to C30 alkyl group, C6 to C30 aryl group Or a combination thereof, in Formulas S-3 and S-4, any one of R 1 to R 4 represents a binding position, and in Formula S-5, any one of R 1 to R 3 represents a binding position. Indicates.
  • Ar 2 is any one of Formulas S-1 to S-5, electron injection and transport characteristics may be adjusted according to each substituent.
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-1.
  • X 1 to X 8 are each independently, -CR'- or N, and R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, at least one of X 1 to X 3 is N, and at least one of X 4 to X 8 is N.
  • the process temperature may be improved due to the lower molecular weight than derivatives such as pyridine, pyrimidine, and triazine having a diphenyl substituent.
  • the compound for an organic optoelectronic device represented by Chemical Formula 1 may be represented by the following Chemical Formula ad-2.
  • X 1 to X 3 are each independently, -CR'- or N, wherein R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to A C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and at least one of X 1 to X 3 is N.
  • thermal stability such as glass transition temperature may be improved due to the introduction of biphenyl having excellent thermal stability, and the non-planarity of molecules may be improved due to the introduction of bulky diphenyl substituents to intermolecular interaction The action can be suppressed.
  • the compound for an organic optoelectronic device may be any one of the compounds represented by Formulas A-1 to A-36. However, it is not limited thereto.
  • the compound for an organic optoelectronic device may be any one of the compounds represented by Formulas B-1 to B-96. However, it is not limited thereto.
  • the compound for an organic optoelectronic device may be any one of the compounds represented by Formulas C-1 to C-49. However, it is not limited thereto.
  • the compound for an organic optoelectronic device may be represented by the following formula D-1 to D-20. However, it is not limited thereto.
  • introducing a functional group having the electronic characteristics is effective for improving the lifespan and driving voltage of the organic light emitting diode.
  • Compound for an organic optoelectronic device has a maximum emission wavelength of about 320 to 500 nm, triplet excitation energy (T1) is 2.0 eV or more, more specifically 2.0 to 4.0 eV range
  • T1 triplet excitation energy
  • the charge of the host having a high triplet excitation energy is well transferred to the dopant, thereby increasing the light emitting efficiency of the dopant and lowering the driving voltage by freely adjusting the HOMO and LUMO energy levels of the material. Because of the advantages it can be very useful as a host material or a charge transport material.
  • nonlinear optical material since the compound for an organic optoelectronic device has photoactive and electrical activity, nonlinear optical material, electrode material, color change material, optical switch, sensor, module, wave guide, organic transistor, laser, light absorber, dielectric and separator It can also be very usefully applied to materials such as (membrane).
  • the compound for an organic optoelectronic device including the compound as described above has a glass transition temperature of 90 ° C. or higher, and a thermal decomposition temperature of 400 ° C. or higher, thereby providing excellent thermal stability. This makes it possible to implement a high efficiency organic photoelectric device.
  • the compound for an organic optoelectronic device including the compound as described above may serve as light emission, electron injection and / or transport, and may also serve as a light emitting host with an appropriate dopant. That is, the compound for an organic optoelectronic device may be used as a host material of phosphorescence or fluorescence, a blue dopant material, or an electron transport material.
  • Compound for an organic optoelectronic device according to an embodiment of the present invention is used in the organic thin film layer to improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, it is possible to lower the driving voltage.
  • one embodiment of the present invention provides an organic optoelectronic device comprising the compound for an organic optoelectronic device.
  • the organic optoelectronic device refers to an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photosensitive drum, an organic memory device, and the like.
  • a compound for an organic optoelectronic device according to an embodiment of the present invention is included in an electrode or an electrode buffer layer to increase quantum efficiency, and in the case of an organic transistor, a gate, a source-drain electrode, or the like may be used as an electrode material. Can be used.
  • Another embodiment of the present invention is an organic light emitting device comprising an anode, a cathode and at least one organic thin film layer interposed between the anode and the cathode, at least any one of the organic thin film layer is an embodiment of the present invention It provides an organic light emitting device comprising a compound for an organic optoelectronic device according to.
  • the organic thin film layer which may include the compound for an organic optoelectronic device may include a layer selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer and a combination thereof. At least one of the layers includes the compound for an organic optoelectronic device according to the present invention.
  • the hole transport layer or the hole injection layer may include a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the compound for an organic optoelectronic device when included in a light emitting layer, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, and in particular, may be included as a fluorescent blue dopant material.
  • FIG. 1 to 5 are cross-sectional views of an organic light emitting device including a compound for an organic optoelectronic device according to an embodiment of the present invention.
  • the organic light emitting diodes 100, 200, 300, 400, and 500 according to the embodiment of the present invention are interposed between the anode 120, the cathode 110, and the anode and the cathode. It has a structure including at least one organic thin film layer 105.
  • the anode 120 includes a cathode material, and a material having a large work function is preferable as the anode material so that hole injection can be smoothly injected into the organic thin film layer.
  • the positive electrode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or alloys thereof, and include zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
  • metal oxides such as ZnO and Al, or combinations of metals and oxides such as SnO 2 and Sb, and poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene] (conductive polymers such as polyehtylenedioxythiophene (PEDT), polypyrrole and polyaniline, etc.), but is not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) may be used as the anode.
  • the negative electrode 110 includes a negative electrode material, and the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic thin film layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof, and LiF / Al.
  • Multilayer structure materials such as LiO 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, and the like, but are not limited thereto.
  • a metal electrode such as aluminum may be used as the cathode.
  • FIG. 1 illustrates an organic light emitting device 100 in which only a light emitting layer 130 exists as an organic thin film layer 105.
  • the organic thin film layer 105 may exist only as a light emitting layer 130.
  • FIG. 2 illustrates a two-layered organic light emitting diode 200 including an emission layer 230 and an hole transport layer 140 including an electron transport layer as the organic thin film layer 105, as shown in FIG. 2.
  • the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140.
  • the light emitting layer 130 functions as an electron transporting layer
  • the hole transporting layer 140 functions to improve bonding and hole transporting properties with a transparent electrode such as ITO.
  • FIG. 3 is a three-layered organic light emitting device 300 having an electron transport layer 150, an emission layer 130, and a hole transport layer 140 as an organic thin film layer 105, and the organic thin film layer 105.
  • the light emitting layer 130 is in an independent form, and has a form in which a film (electron transport layer 150 and hole transport layer 140) having excellent electron transport properties or hole transport properties is stacked in separate layers.
  • FIG. 4 illustrates a four-layered organic light emitting diode 400 in which an electron injection layer 160, an emission layer 130, a hole transport layer 140, and a hole injection layer 170 exist as an organic thin film layer 105.
  • the hole injection layer 170 may improve adhesion to ITO used as an anode.
  • FIG. 5 shows different functions such as the electron injection layer 160, the electron transport layer 150, the light emitting layer 130, the hole transport layer 140, and the hole injection layer 170 as the organic thin film layer 105.
  • the five-layer organic light emitting device 500 having five layers is present, and the organic light emitting device 500 is effective in lowering the voltage by separately forming the electron injection layer 160.
  • the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, and the hole injection layer 170 forming the organic thin film layer 105 and their Any one selected from the group consisting of a combination includes the compound for an organic optoelectronic device.
  • the compound for an organic optoelectronic device may be used in the electron transport layer 150 including the electron transport layer 150 or the electron injection layer 160, and the hole blocking layer (not shown) is included in the electron transport layer. It is desirable to provide an organic light emitting device having a simplified structure because it does not need to be formed separately.
  • the compound for an organic optoelectronic device when included in the light emitting layers 130 and 230, the compound for an organic optoelectronic device may be included as a phosphorescent or fluorescent host, or may be included as a fluorescent blue dopant.
  • the above-described organic light emitting device includes a dry film method such as an evaporation, sputtering, plasma plating and ion plating after forming an anode on a substrate;
  • the organic thin film layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode thereon.
  • a display device including the organic light emitting diode is provided.
  • Compound A-10 was synthesized through the following synthesis reactions.
  • Compound B-1 was prepared through the following synthesis method.
  • Compound B-57 was prepared by the following synthesis method.
  • Compound C-1 was prepared in the following manner.
  • Compound D-4 was prepared in the following manner.
  • the glass substrate coated with ITO (Indium tin oxide) 1500 thin film was washed with distilled water ultrasonic. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.
  • a solvent such as isopropyl alcohol, acetone, methanol and the like
  • HTM see material structure below
  • HTM was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 1200 ⁇ .
  • Example 1 The material synthesized in Example 1 was used as a host on the hole transport layer, and PhGD (see the following figure) was doped with phosphorescent green dopant to form a light emitting layer having a thickness of 300 ⁇ by vacuum deposition.
  • BAlq (Bis (2-methyl-8-quinolinolato-N1, O8)-(1,1'-Biphenyl-4-olato) aluminum] 50um and Alq3 [Tris (8-hydroxyquinolinato) aluminium] 250 ⁇ Laminated sequentially to form an electron transport layer.
  • An organic light emitting device was manufactured by sequentially depositing LiF 5 ′ and Al 1000 ′ on the electron transport layer to form a cathode.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using Example 2 (B-1) instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using Example 3 (B-57) instead of Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using CBP instead of Example 1.
  • the current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the brightness, current density, and voltage measured from (1) and (2) above.
  • the light emission characteristics of the hosts manufactured in Examples 6 to 8 are lower in driving voltage and higher in power efficiency than CBP of Comparative Example 1.

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Abstract

L'invention concerne un composé pour dispositif opto-électronique organique, un élément électroluminescent organique comprenant ce composé, et un dispositif d'affichage comprenant l'élément électroluminescent organique. Elle concerne un composé représenté par la formule chimique (1) ci-dessous, destiné à un dispositif opto-électrique organique et permettant de fabriquer un élément électroluminescent organique ayant une excellente durée de vie, en ce qu'il présente une stabilité électrochimique et thermique supérieure, ainsi qu'un rendement lumineux élevé, même sous faible tension de commande.
PCT/KR2012/011429 2011-12-26 2012-12-26 Composé pour dispositif opto-électronique organique, élément électroluminescent organique comprenant ce composé, et dispositif d'affichage comprenant l'élément électroluminescent organique WO2013100538A1 (fr)

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